I will be renting a cottage for a week next month and bringing my 11 year old grandson and his friend along for the week. We do this usually every year and would leave the kitties behind at home with a daily visit from a pet service for feeding and litter tidy up.
This year, one of our cats has had numerous medical problems and is still a bit shakey from a neuro condition, so we decided he would come along to the cottage with us because he requires 4 different meds each day and also must be monitored for his bowel movements. I know the sitter who always takes our home for us from the service, and she is very good, but because of this guy's condition, would feel better if I was supervising his care and knew for sure that he was getting his meds etc.
My concern, and this is really starting to cause me anxiety, is the cottage is small, with a wooden screen door type closure. I plan to bring a play pen with me to keep Quincy in on the deck when we are outside, with a netting over top to keep him protected (he cannot really jump at this point, so he will not be able to jump out), but I am having disaster nightmares of him slipping out the door with the kids running in and out. I plan to sit them down and be tough about watching the door, but boys are boys and outside is outside. A big thing for city boys. At home, Quincy never shows any desire to get outside, but I am afraid in a new enviroment he may be frightened and bolt. This cottage is really in the woods.
Any suggestions about how to handle this? I am considering just trying to have faith in the sitter who will be coming in for my other 3 kitties, but it has really been a tough 6 months for this poor guy and I fear any backsliding by him health wise if he is not continually watched. I have tried to find someone to come in and "house sit", but the cost for the service to do this for a week is almost more than the cost of the cottage for a week and we do not have any family or really know our neighbours, so there is no one to ask.
Feedback? Suggestions? Just plain comments to try and relieve some anxiety?
Thanks.

I feel that your cat will be more nervous in a new environment, and probably better off left at home. Little kids are not to be trusted in keeping the cat in. I think the stress will be worse. When I bring up my terrier dog, which would run away at the slightest chance to hunt, I do not enjoy my stay there and I am a mess worrying about it the whole weekend. That's my opinion.

If you do decide to take him along maybe you could keep him on a very long lead in the cottage. Long enough that he isn't restricted and has the run of the place but can't escape either. I don't know if that would be a safety concern or not. I would never leave Coooper on a leash if I went out but if you're right there to supervise him it might be ok?

What about setting up a sort of "vestibule" with baby gates or plywood or something like that around the door (inside or out), so that there isn't that direct access to the outside. The humans can step over it or slide it open and it creates just that little extra delay to prevent your cat from making a run for it.

Thanks everyone for the advise. I called my vet this morning to see if she knew anyone who would be able to stay with all the cats while we were at the cottage, and while talking with the vet assistant who answered the phone, she agreed to come in twice a day while we were gone and see to them!
I was so happy. Her mother lives close by so she could come before and after work and the added bonus is she know the guys and is experienced with the meds for Quincy.
It is such a relief for me. Now I may actually be able to relax for the week we are gone and not have to worry about Quincy bolting and getting lost in the woods or being at home and not getting all his meds on schedule